HCID 55285668, compound → HCID 67052527, compound

Participants

Reaction Conditions

Reaction Steps

Nitromalonaldehyde sodium salt monohydrate (1.46 g, 9.29 mmol) was added to crude 2-(5-amino-1H-pyrazol-3-yloxy)ethanol (3.28 g) with salts (1.33 g, 9.29 mmol theoretical) in acetic acid (10 mL). This was heated at 90° C. for 2 hours. The cooled reaction mixture was diluted with water, and the mixture was extracted twice with DCM containing 25% IPA. The organic extracts were dried over magnesium sulfate, filtered, and evaporated to yield regioisomer 2-(6-nitropyrazolo[1,5-a]pyrimidin-2-yloxy)ethanol (0.77 g, 3.43 mmol) as a solid. The 2-(6-nitropyrazolo[1,5-a]pyrimidin-2-yloxy)ethanol (460 mg, 2.9 mmol) was suspended in water (40 mL), treated with saturated aqueous sodium bicarbonate (2 mL), and the mixture was refluxed for 2 hours. The cooled reaction mixture was extracted three times with DCM containing 25% IPA. The organic extracts were dried over magnesium sulfate, filtered, and evaporated to an oil. The crude material was purified by column chromatography with ethyl acetate to provide 2-(5-nitro-1H-pyrazolo[3,4-b]pyridin-3-yloxy)ethanol (60 mg, 0.27 mmol, 2.9% yield) as a solid.

Provenance & Evidence